Trifluoroacetic acid → 4-Pentafluoroethyloxy-piperidine

HRID 341522Notes

Reaction equation

HRID 341522 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:26])([F:25])[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1>C(Cl)Cl>[F:26][C:9]([F:8])([F:25])[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21906044HCID 21906044, compound

Product 1

HCID 246896794-Pentafluoroethyloxy-piperidineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.15 mL) was added dropwise to a solution of tert-butyl 4-(2,2,2-trifluoroethoxy)piperidine-1-carboxylate (prepared in an analogous manner to Intermediate 203, 1.14 g, 4.0 mmol) in DCM (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 16 h. The mixture was then concentrated under vacuum, the crude residue was dissolved in water and product was extracted with diethylether (2 times). The aqueous phase was basicified to pH 10 using solid potassium carbonate and extracted with DCM (4 times). The organic extracts were combined, dried over sodium sulfate and concentrated under vacuum to afford the title compound (610 mg, 83%). 1H NMR (300 MHz, CDCl3) δ ppm 3.84 (2H, q), 3.53 (1H, m), 3.10 (2H, m), 2.61 (2H, m), 1.76 (2H, m) and 1.54 (2H, s).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. dissolutionthe crude residue was dissolved in water
  3. extractionproduct was extracted with diethylether (2 times)
  4. extractionextracted with DCM (4 times)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-81e50062f7c949c7ac6769398bb5af29
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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